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Concise and Practical Asymmetric Synthesis of a Challenging Atropisomeric HIV Integrase Inhibitor.
Fandrick KR1,
Li W2,
Zhang Y2,
Tang W2,
Gao J2,
Rodriguez S2,
Patel ND2,
Reeves DC2,
Wu JP2,
Sanyal S2,
Gonnella N2,
Qu B2,
Haddad N2,
Lorenz JC2,
Sidhu K2,
Wang J2,
Ma S2,
Grinberg N2,
Lee H2,
Tsantrizos Y3,
Poupart MA3,
Busacca CA2,
Yee NK2,
Lu BZ2,
Senanayake CH2.
- 1
- Chemical Development, Boehringer-Ingelheim Pharmaceuticals Inc. 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT 06877-0368 (USA). keith.fandrick@boehringer-ingelheim.com.
- 2
- Chemical Development, Boehringer-Ingelheim Pharmaceuticals Inc. 900 Ridgebury Road, P.O. Box 368, Ridgefield, CT 06877-0368 (USA).
- 3
- Research and Development, Boehringer Ingelheim (Canada) Ltd. 2100 Cunard Street, Laval, Québec H7S 2G5 (Canada).
Abstract
A practical and efficient synthesis of a complex chiral atropisomeric HIV integrase inhibitor has been accomplished. The combination of a copper-catalyzed acylation along with the implementation of the BI-DIME ligands for a ligand-controlled Suzuki cross-coupling and an unprecedented bis(trifluoromethane)sulfonamide-catalyzed tert-butylation renders the synthesis of this complex molecule robust, safe, and economical. Furthermore, the overall synthesis was conducted in an asymmetric and diastereoselective fashion with respect to the imbedded atropisomer.
© 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
KEYWORDS:
Suzuki couplings; acylation; asymmetric synthesis; phosphine ligands; tert-butylation
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